TY - JOUR
T1 - N-Phosphinyl Imine Chemistry (I): Design and Synthesis of Novel N-Phosphinyl Imines and their Application to Asymmetric aza-Henry Reaction
T2 - Design and Synthesis of Novel N-Phosphinyl Imines and their Application to Asymmetric aza-Henry Reaction
AU - Pindi, Suresh
AU - Kaur, Parminder
AU - Shakya, Gaurav
AU - Li, Guigen
PY - 2011/1
Y1 - 2011/1
N2 - Novel chiral N-phosphinamide and N-phosphinyl imines have been designed, synthesized and applied to asymmetric aza-Henry reaction to give excellent chemical yields (92%- quant.) and diastereoselectivity (91% to >99%de). The reaction showed a great substrate scope in which aromatic/aliphatic aldehyde- and ketone-derived N-phosphinyl imines can be employed as electrophiles. The chiral N-phosphinamide can be stored at room temperature for more than 2 months without inert gas protection, and chiral N-phosphinyl imines were also proven to be highly stable at room temperature for a long period under inert gas protection. The N-phosphinyl group enabled the product purification to be performed simply by washing crude product with EtOAc and hexane. This reaction joined other eight GAP (Group-Assistant-Purification) chemistry processes that were developed in our laboratories. The absolute configuration has been unambiguously determined by converting a β-nitroamine product into a known N-Boc sample.
AB - Novel chiral N-phosphinamide and N-phosphinyl imines have been designed, synthesized and applied to asymmetric aza-Henry reaction to give excellent chemical yields (92%- quant.) and diastereoselectivity (91% to >99%de). The reaction showed a great substrate scope in which aromatic/aliphatic aldehyde- and ketone-derived N-phosphinyl imines can be employed as electrophiles. The chiral N-phosphinamide can be stored at room temperature for more than 2 months without inert gas protection, and chiral N-phosphinyl imines were also proven to be highly stable at room temperature for a long period under inert gas protection. The N-phosphinyl group enabled the product purification to be performed simply by washing crude product with EtOAc and hexane. This reaction joined other eight GAP (Group-Assistant-Purification) chemistry processes that were developed in our laboratories. The absolute configuration has been unambiguously determined by converting a β-nitroamine product into a known N-Boc sample.
KW - Aza-Henry reaction
KW - Chiral N-phosphinamide
KW - GAP (Group-Assistant-Purification) chemistry
KW - N-phosphinyl imines
UR - http://www.scopus.com/inward/record.url?scp=78650133416&partnerID=8YFLogxK
U2 - 10.1111/j.1747-0285.2010.01047.x
DO - 10.1111/j.1747-0285.2010.01047.x
M3 - Article
C2 - 21134217
SN - 1747-0277
VL - 77
SP - 20
EP - 29
JO - Chemical Biology & Drug Design
JF - Chemical Biology & Drug Design
IS - 1
ER -